Issue 14, 2014

Enantioselective 1,4-additions of ClMeAl(CH[double bond, length as m-dash]CHR) (R = alkyl, alkenyl, Ph) to cyclohexenones

Abstract

Chloromethylvinyl alanes (E)-ClMeAl(CH[double bond, length as m-dash]CHR) prepared directly from terminal alkynes undergo 1,4-addition to cyclohexenone and 3-methylcyclohexenone in moderate to good yield (30–70%) and good to excellent stereoselectivity (80–98% ee) using readily available copper(I) sources and chiral ligands.

Graphical abstract: Enantioselective 1,4-additions of ClMeAl(CH [[double bond, length as m-dash]] CHR) (R = alkyl, alkenyl, Ph) to cyclohexenones

Supplementary files

Article information

Article type
Communication
Submitted
25 Oct 2013
Accepted
19 Nov 2013
First published
07 Jan 2014

Chem. Commun., 2014,50, 1655-1657

Enantioselective 1,4-additions of ClMeAl(CH[double bond, length as m-dash]CHR) (R = alkyl, alkenyl, Ph) to cyclohexenones

D. Willcox, S. Woodward and A. Alexakis, Chem. Commun., 2014, 50, 1655 DOI: 10.1039/C3CC48191C

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